Design and synthesis of 4-aryl-4-oxobutanoic acid amides as calpain inhibitors

Bioorg Med Chem Lett. 2009 Jan 15;19(2):502-7. doi: 10.1016/j.bmcl.2008.11.030. Epub 2008 Nov 14.

Abstract

The involvement of mu-calpain in neurological disorders, such as stroke and Alzheimer's disease has attracted considerable interest in the use of calpain inhibitors as therapeutic agents. 4-Aryl-4-oxobutanoic acid amide derivatives 4 were designed as acyclic variants of mu-calpain inhibitory chromone and quinolinone derivatives. Of the compounds synthesized, 4c-2, which possesses a 2-methoxymethoxy group at the phenyl ring and a primary amide at the warhead region most potently inhibited mu-calpain (IC(50)=0.34 microM). Our findings suggest that the 4-aryl-4-oxobutanoic acid amide derivatives should be considered as a new family of mu-calpain inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Butyric Acid / chemical synthesis
  • Butyric Acid / chemistry*
  • Butyric Acid / pharmacology*
  • Calpain / antagonists & inhibitors*
  • Cysteine Proteinase Inhibitors / chemical synthesis
  • Cysteine Proteinase Inhibitors / chemistry*
  • Cysteine Proteinase Inhibitors / pharmacology*
  • Drug Design

Substances

  • Amides
  • Cysteine Proteinase Inhibitors
  • Butyric Acid
  • Calpain